


Behind bars

by gabrielsbutt



Category: Supernatural
Genre: Alternate Universe, M/M, Prison AU
Language: English
Status: In-Progress
Published: 2015-07-26
Updated: 2015-08-15
Packaged: 2018-04-11 07:57:23
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 12
Words: 12,561
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4427525
Author URL: https://archiveofourown.org/users/gabrielsbutt/pseuds/gabrielsbutt
Summary: <blockquote class="userstuff">
              <p>Prison doesn't exactly conjure up thoughts of romance, however in Castiel's case, it most certainly does. Seeing as the next thirty years of Castiel's life will be spent behind bars, he seeks to make the best of his dire situation. Cue: Doctor Dean Winchester.</p>
            </blockquote>





	1. Prologue

**Author's Note:**

> This fic is loosely inspired by the TV series Prison Break, so if you've seen that you'll definitely see some crossovers and similarities as the fic progresses. This is like my first long(ish) destiel fic so bear with me if it's kind of crap in places. I doubt I'm gonna beta it so all mistakes will by my own. Also just want to add, that this is fiction and so details regarding prison life will most likely not be accurate. Anyways, I really love this concept, so I'm hoping that you guys will too and that it turns out okay! Enjoy reading and feedback is always welcomed.

“HANDS UP! PUT YOUR HANDS WHERE I CAN SEE THEM!”

The voices barked. It was over. Castiel’s jaw clenched, two shot guns came clattering to the floor, he slowly lifted his hands in defeat.

What followed was a confused blur of colours and sounds and ecstasy. People crying, cops shouting orders, alarms sounding- everything was so very alive. The flashing blue and red lights of the police cars only served to enthral Castiel rather than scare him. The cold metal cuffs fixed firmly round his wrists were a sudden reminder of his destination. Prison.

-

The trial for Castiel’s case was a fairly smooth process, the judge not taking long to come to a decision regarding his sentencing.  
“Due to your violent conduct, attempted armed robbery of a bank and most significantly, the murder you committed; I am recommending a prison sentence of twenty years minimum, with a possible chance of parole on good behaviour.”

The judge concluded, fixing Castiel with a piercing stare. “The fear and pain you have inflicted on so many lives is absolutely devastating, and I hope you will use the time you will be serving wisely, to reflect upon your actions. You have committed a great injustice to society Mr Novak.” The judge pursed her lips and shook her head slowly, then indicated to the guard to take Castiel away.

And prison life began.


	2. Chapter 2

The first day at U.S Penitentiary Marion was an interesting one. After the countless security checks and rub downs, Cas was finally walked to his cell; he clutched his few and restricted belongings tightly to his chest, suddenly feeling very small. He walked briskly, thankful for the guard’s tight grip around his arm, avoiding any eye contact with the other inmates around him. They soon reached the cell Castiel would be inhabiting; the guard barked the command for the cell door to be opened “in here,” the guard said, roughly nudging Castiel into the cell.

  
“CELL 67 CLOSE!” The guard shouted, the metal bar door clanked shut.

  
Cas gulped, acutely aware of the other presence in his cell. His cellmate. The other man had his legs dangling over the side of the bunk, and Cas could feel his eyes boring into him. Deciding it was better that he introduced himself rather than make himself vulnerable, he slowly raised his eyes to meet the man’s.  
To his relief, and surprise; the eyes that met his were friendly and welcoming. “Loosen up sweetie.” The man said with a grin, Cas swiped a tongue across his lips and nodded in acknowledgement, but he still couldn’t mask the evident fear in his eyes. The man jumped off his bunk and leaned in close to Cas, “You go around with a face a like that and they’ll make you their bitch.” He whispered harshly into Castiel’s ear. Cas’ jaw tightened, not wanting to find out what the anonymous “they” implied.

  
“Right,” he said shortly, nodding. “Name’s Castiel.”

  
“Gabe.” The man replied, holding out his hand, Cas was hesitant at first but figured there was definitely no harm in befriending his cellmate, and shook Gabe’s hand firmly. “You’ll get used to this soon enough Cassy.” Gabe assured. “Just make sure you stay with the right crowd.” He warned in a slightly darker tone.  
Gabe proved correct, it didn’t take Castiel all that long to adjust to life behind bars. He learnt quickly that inmates were short tempered and easy to get on the wrong side of.

-

2 PM — hourly outdoor session; all inmates from Castiel’s wing were escorted to the prison grounds. Cas stuck close to Gabe, figuring that that would be his best move, seeing as he was fairly alone being the 'new kid.' As soon as the inmates were outside they quickly split themselves off into groups, usually dominated by race.  
Gabe leant in close to his ear, “you don’t mess with them, they won’t mess with you,” he whispered, looking in the direction of a group of black guys, who were eyeing Castiel questionably (the latter obviously allowing his gaze to linger for a little too long.) Cas nodded quickly, keeping his head down and scuffing his foot along the turf of the grounds.

Gabe quickly walked Cas through some general prison knowledge, educating him on the ways things went down in the penitentiary. Their conversation was not long disrupted by the intrusion of a small, lean guy, a good few years older than either Cas or Gabe, with grey hair and a twisted smile. “Hello pretty boy,” he greeted Cas, but it didn’t seem all that sincere. “Not often that we get a fine specimen like you inside these walls,” he noted, very obviously checking Castiel out. Cas rolled his eyes and grimaced, typical that he’d attract the weirdos.

  
“Leave it out M.” Gabe clipped in, fixing the smaller man with a hard stare.

  
‘M’ laughed, “c’mon Gabe, don’t have him all for yourself,” he moved in closer to Cas so that he was practically breathing down his neck, “always nice to share,” he added, licking his lips.

  
“If you think for a moment you’re going to lay a hand on me, you have another thing coming.” Castiel retorted through gritted teeth. ‘M’’s eyes widened and he looked around trying to gain the attention of the other inmates.

  
“This one’s got a mouth on him!” he called out, pointing accusingly at Cas. A few inmates turned around, but none seemed to respond, that was until Castiel noticed one guy walking right over towards them.

  
“I always get what I want.” ‘M’ said with a grin, rubbing his hands slowly together. “Don’t think you can get away from me that easily.” He reached out to touch Castiel, but did not account for Castiel’s excellent reflexes, and as he did so, Castiel’s fist made heavy contact with his face, causing him to recoil with a grunt, clutching his face in pain.

  
“Jesus Cas!” Gabe exclaimed, pulling Cas back, and looking around quickly to see if the guards had noticed. Luckily, they hadn’t. But the man who had been approaching them had, and was now eyeing Castiel with interest. He moved in towards them, pushing ‘M’ firmly away. “Beat it.” He hissed at the small man, to which the man quickly scurried away.  
“You can throw a good punch.” The man said with a smile, Cas noted the man’s accent- British.

  
“Crowley.” The man said, holding out his hand, Cas shook it firmly.

  
“Castiel.”

  
“Castiel,” the man rolled the name off his tongue, “if you want people like him to leave you alone, you gotta have a reputation.” He paused, staring at Cas, trying to figure him out. “I can give you that. Stay by me and you’ll have no more trouble, I assure you.” He raised an eyebrow at Cas, nodding to the space beside him. Cas soon got the idea; he was not about to blindly agree to being someone's bitch. “Thank you, but I’ll have to decline.”

  
“Decline? Really? Are you sure?” Crowley asked, his tone darker.

  
“Certain.” Cas replied decidedly.

  
“Bad move Blue Eyes.” Crowley shook his head. “Bad, bad move.” He muttered as he walked away, and the guards whistle sounded the end of outdoor time.

-  
“CELL 67 OPEN!”

  
The door to Castiel’s cell slid open with a jolt.

  
“Castiel Novak.”

  
“Yes?” Cas said, standing up from his bed.

  
The prison officer indicated for Cas to come closer. “Doc needs to see you, routine medical check-up for the newbies.” He informed Cas. Cas nodded in acknowledgment. “Come with me,” the officer instructed, taking Castiel’s arm and calling the command for the cell door to be closed.

  
Cas heaved out a long sigh. It was going to be a long day.


	3. Chapter 3

“Doc, inmate 205. Castiel Novak.” The officer said as he lead Castiel into a clinical yet welcoming looking room.

  
“Ah yes,” a man, similar age to Cas responded- Cas recognised him as the doctor, wearing a white overcoat and carrying a clipboard. He walked towards Cas, lifting his gaze from the clipboard to Castiel and smiled warmly at him. “Thank you officer, I can take it from here.” The doctor said assuringly. The officer nodded, releasing Cas and walking out the door, the doctor closed it behind him.

  
“Could you sit down there for me,” the doctor said softly, gesturing to a chair that sat against a wall. Cas nodded and quickly sat down, from his new position he could get a better look at the very attractive doctor, without it being too obvious; the doctor's attention currently being occupied by whatever was on the clipboard, giving Cas ample time to admire him.

  
“So, Castiel, you're diabetic?” the doctor asked, still looking at the clipboard, writing something down.

  
“Indeed I am." Castiel responded with a grin.

The doctor looked up, meeting Castiel's gaze, allowing it to linger for perhaps a little longer than what would be considered professional. Cas cocked an eyebrow, a smile playing on his lips and could've sworn the doctor blushed a little, before hurriedly looking back down at his clipboard.  
“As far as your records show, that's your only medical condition. No psychiatric problems have been recorded either. Is that correct?” The doctor looked up again, but his gaze was harder now.

  
“Do I look like a nutcase Doc?” Cas asked teasingly.

  
“That's not what I was saying. I just need to confirm that your records are correct.” The doctor said, his jaw set, Castiel's charm apparently having no obvious effect on him.

  
“As far as I know they are.” Cas replied, more sincerely this time. The doctor nodded and scribbled something down. As he did so Castiel's eyes wandered over the doctor, catching sight of the name tag pinned to his pocket: Dr Dean Winchester.  
“Dean, nice name.” Castiel announced with a smirk. The doctor looked up quickly, his confusion soon turning to realisation as he glanced at his name tag and fixed Cas with a hard stare.

  
“It's Doctor Winchester to you.” He said firmly. “Clear?”

  
Cas nodded. Dean set down his clipboard and walked over to the far side of the room, pulling open a drawer and taking out the necessary items to assemble an insulin shot.  
“I'll schedule daily appointments for your insulin shots.” Dean said as he walked back towards Cas.

  
“Thank you." Cas nodded.

  
“Can you hold out your arm for me please,” he asked, sitting down on the chair beside Cas, the insulin needle in one hand. Cas complied quickly, stretching out his arm for the doctor.

  
Dean slid the needle into the correct vein with practiced ease, and the procedure was quickly over.

  
“That'll be all. See you tomorrow.” Dean said, matter-of-factedly, pressing a small buzzer to notify an officer that Castiel was ready to be escorted back to his cell.

  
“Thanks Doc, later.” Cas said with a smile, his fingers very lightly grazing across the doctors hand. Dean quickly moved his hand away, face reddening, he nodded in acknowledgement, avoiding eye contact with Cas.  
Cas smiled, Dean may act like he had a tough exterior, but Cas always loved a challenge. And given his current predicament, it would be a particularly difficult one.  
“Novak, move your ass.” The officers stern voice broke Castiel's line of thought. He followed the officer out of the room, stealing himself one last look at the doctor.  
Cas smiled, never in his life had he been so thankful to be diabetic.

-

“You know much about the doctor” Cas asked lazily, lying on his bed as he mentally played through his brief encounter with Dean.

  
“Not really.” Gabe responded from the top bunk, “why?”

  
“I like him.” Cas replied confidently.

  
Gabe stuck his head over the bunk and looked down at Cas, scrunching up his nose, “you have the hots for the doctor? Isn't that just typical.” He laughed, clapping his hands together and jumping off the bunk.

  
Cas rolled his eyes at Gabe.

  
“C'mon man, out of all the people you could have had in this prison, you got for doc? I mean, I'll give it to you, he's hot as hell, but...really?” Gabe shook his head and laughed again, slapping his thighs.

  
“You don't have to tell the whole world.” Cas hissed, “I only wanted to see if you knew anything about him. No need to be so dramatic.”

  
Gabe collected himself, “all I know is that he's fairly new here, his name's Dean Winchester and he's one of the few medics at the prison. That's it.” He said, looking at Cas, who nodded, determined to find out more about Dr Dean Winchester.

-

“Why's he staring at me like that?” Castiel asked, looking out of his cell. Gabe followed his line of sight to see Crowley in the cell directly opposite, fixing Castiel with a piercing stare.

  
“Why'd you think?" Gabe asked, raising an eyebrow.

  
"I pissed him off." Cas mumbled.

  
"Damn right you pissed him off. And that's not exactly the best move to make when it's your first day at prison.”

  
“I didn't want to be his bitch.” Cas retorted, flicking his eyes from Crowley's deadly stare to Gabe's softer one.

  
“Understandable, but you're on his hit list now. He's going to do everything in his power to make your life miserable.” Gabe responded with a knowing sigh.

  
“Just what I need,” Castiel muttered, resting his head in his hands dejectedly.

  
“If you try and befriend some other inmates, someone with influence, you could avoid too much trouble.” Gabe volunteered.

  
Cas lifted his head from his hands, “like who?”

  
Gabe paused before responding.

 

“Gadreel.”

**Notes for the Chapter:**

> Whatchya guys thinking? You liking? I really wanted to include Gadreel into the fic because I think he's a badass character and that's what prison is all about right? Hope you're enjoying!


	4. Chapter 4

“RISE AND SHINE!” The prison officers chimed, drumming their batons against the prison cell doors. Cas awoke with a start, it took a few moments before all the events of yesterday caught up with him. 

He was in prison. And this was day two. Day two out of seven thousand, three hundred and three. 

Cas chuckled, there was really no use in marking off the days. 

“What you giggling about?” Gabe asked with a smile, turning from the small basin where he was splashing water onto his face. 

“Just how long my sentence is,” Cas said with a yawn. 

“That's not something inmates usually chuckle about.” Gabe replied, a twinkle in his eye, patting down his face with a towel. 

Cas shrugged, “might as well make a joke out of it while I can.” He said with a stretch, before getting off of his bed and walking over to the small basin. 

“Fair point, how long you got anyways?” Gabe asked curiously. 

Cas ran the tap and grabbed his toothbrush, “twenty years, minimum.” He said, squirting some toothpaste onto the brush. 

“Jesus Christ Cassy, what the hell did you do?”

Cas sighed, “I tried to rob a bank, and failed, obviously.”

“Twenty years? Just for robbing a bank?” Gabe asked, a disbelieving air in his voice. 

Cas rinsed his mouth and spat, rubbing the pad of his thumb across his lips before turning to face Gabe. “No, I uh, I shot a guy. A security guard. Killed him.” His voice was flatter now, he bit his lip and tightened his jaw. 

“Damn,” Gabe said with a gasp, “I mean there's guys in here who've committed far worse crimes than that. But, I didn't take you for a killer.”

“I'm not a killer!” Cas snapped back, sighing. “Look, I don't want to talk about it.” He clenched his jaw, eyes cast to the ground.

Gabe nodded, but the uncomfortable silence between them was thankfully disrupted by the breakfast bell. 

-

Breakfast wasn't quite as straightforward as Cas had anticipated. Sure, the 'getting breakfast' part was fine, even though breakfast was nothing to write home about: simply some buttered toast and a measly rash of bacon. 

It was finding somewhere to sit that was difficult, everyone had occupied their own table, 'their patch' and you couldn't exactly just come along and sit down with them. Unless you wanted a fist to your face, or worse, a makeshift blade to your throat. 

There were a few tables with some empty seats, but the people on them were not people Cas wanted to associate with. One table seemed to be reserved for the outcasts, at least from what Cas could tell; as the inmates seated there were all from different races, their only unifying factor being the bat-shit crazy expression on their faces. 

Another table had a few lean, shady looking guys seated, creepy looking guys. Cas shuddered. 

“You don't want to sit over there,” a deep voice said behind him. “That's where the animals sit, the wrong-uns...so unless you belong with them, I'd suggest somewhere else.” Cas turned to see the owner of the voice. A tall, broad man stood behind him, his face was conveying very little emotion. 

“Understood,” Cas said firmly. 

The corner of the other man's lip twitched upwards very slightly, “follow me.” It was an instruction rather than an offer, and Cas didn't fancy seeing what happened if he refused. 

The man walked over to a table with two empty seats on one end of it. He sat down on one and Cas followed suit. 

“Your new?” The man asked, biting into his toast. 

“Yes, came in yesterday.” 

The man nodded, chewing thoughtfully, “what you in for?”

“Attempted robbery and murder.” Cas replied, quieter now, staring down at his plate. 

“Sound like my kind of guy,” the man smirked. 

Cas looked up, squinting at the man, trying to work out exactly what his intentions were. 

“I'm Gadreel. Figure you'll hear about me soon enough anyway; might as well introduce myself.” 

“Castiel.”

“Interesting name,” Gadreel commented. 

“As is yours.” Castiel threw back, mouth curving into a smile. 

Gadreel chuckled, although it wasn't at all genuine. “I didn't call you over to sit with me so we could talk about names, so I guess you're wondering why?”

Cas nodded, head tilted, Gadreel leaned forward, chewing slowly on a piece of bacon. 

“How would you feel about working with me Castiel? Being my...accomplice?” He asked, swiping a tongue across his lips and looked at Cas questionably. 

Castiel's brows furrowed, “could I ask why you haven't already acquired an accomplice?”

Gadreel sat back in his chair and smiled, “oh I have, I've had several before you. But for various reasons, they didn't work out. However I can assure you, as long as you don't double cross me, you'll have nothing to worry about.” He crossed his arms together, watching Castiel's expression closely. 

“Why me?” Cas squinted. 

“You intrigue me, I think we'd make a good team Castiel.” Gadreel responded monotonously. 

Cas looked away, chewing on his lip in thought. 

“Pack it in boys! Breakfasts over!” an officer from the back of the hall shouted. 

Gadreel stood up slowly, scraping his chair across the floor. Cas followed. 

“So, what will it be Castiel?” Gadreel asked, leaning in close to him as they filed in line to be escorted back to the cell block. 

Cas paused, sighing. “Yes.” He responded, his voice clipped. 

“Wise man. See you round.” 

-

“This Gadreel, what do you know about him,” Cas asked as he flicked through the pages of a worn comic book, head resting against the thin pillow of his bed. 

“You don't wanna mess with Gadreel,” Gabe returned, making a tutting sound with his mouth. “He's nasty work, if you're on the wrong side of him.”

“Why?” 

“Do you know what he's in for?” Gabe asked, jumping off from the bunk. 

“Enlighten me.” Cas rested the book flat on his stomach and turned to look at Gabe. 

“Six counts of murder. And the worst part, they were his family. His estranged family, apparently.” Gabe said, shaking his head sorrowfully. 

“I agreed to be his accomplice,” Cas relplied, sitting up. 

“You did? Well, you know you're in that for good now. No double-crossing him.” Gabe warned. 

“I know. I'll be careful, but I could use his reputation.” 

Gabe nodded. “Just stay safe Cassy.” 

-

“Ah, Castiel, take a seat.” Dean raised his eyebrows as Cas entered the doctors room. 

“Doctor Winchester,” Cas acknowledged, moving his way towards the chair. 

Dean quickly set about making up the insulin shot, his back to Castiel. “How's your second day behind bars been?” He asked, fixing up the shot. 

“Good thanks,” Cas replied, “hows your day been, doctor?”

Dean turned around, a brief smile playing on his lips. “Busy, but good. Thank you.” 

“Glad to hear it,” Cas smirked, holding out his arm as Dean prepped the needle. 

Dean eyed Castiel with some uncertainty, sitting down beside him. “You keeping out of trouble?” Dean asked as he slid the needle into Castiel's arm. 

“As much as you can when you're in a prison.” Cas replied, looking curiously at Dean, who seemed to be avidly avoiding any sort of eye contact with him. 

“Good,” Dean said curtly, patting down Castiel's arm. “Try and keep it that way,” he added, looking at Cas now. There was genuine concern in his expression, Cas didn't have any witty comebacks this time, simply nodded. 

“Well, you're all done. Have a good day Castiel.” Dean said, pressing the buzzer. 

“You too Doc,” Cas replied softly, standing up as the officer entered the room to escort Castiel away. 

Cas stole a glance behind him as he was walked away, wanting to add as much as he could to his visual bank of 'Dean Winchester' as he possibly could; to his surprise, Dean was looking right at him. Of course, he looked away quickly, as soon as he met Castiel's gaze, brushing down his overcoat and turning away. 

But Cas had seen. And that was enough

**Notes for the Chapter:**

> I promise as the chapters progress there will be more Dean/Cas interaction but I also love writing about prison life. What do you think of Gadreel? Yay? Nay? I think I might have some Dean POV chapters at some point as well. Anyways, thank you for reading! (I'm gonna try and update on a weekly basis if not before, just fyi, depending on how quickly I get the chapters written.)


	5. Chapter 5

“Break it up inmates!” A stern voice called from behind the fence. They were in the outdoor area of the penitentiary, for the hourly session; the sun was casting a soft glow over the turf, and for a few moments, it didn't feel like prison. That was quickly disrupted by raised voices throwing violent threats at one another. Cas turned around to identify the commotion that the officer had been addressing. 

To his dismay, Crowley stood there, only about ten feet from Cas; face contorted in anger, having just thrown a punch at an inmate, who was now staggering away. His head snapped towards Castiel's direction, and upon seeing him, his face expression turned into an ugly grimace. 

Cas stepped back a few paces, where the hell was Gadreel? “Gabe!” He hissed at the smaller man, who was sitting on a bench beside him, chewing his lip anxiously. Gabe was all too well accustomed to how these fights went down, and for that reason, knew he was powerless to help in any way. 

Crowley stormed towards Cas, fists balled tightly by his sides. Cas backed away as far as was possible in an enclosed area, so that his back was pressed up against the wire mesh fence. Before he had any time to react, Crowely's hand was round his throat, fingers tightening. 

“Hello again Blue Eyes,” he greeted in a hoarse whisper. “Funny you know, usually, when you piss an inmate off, you have the sense to bloody stay away from them. But not you...” Crowley chuckled, his grip around Castiel's throat tightening even more so.

“I don't want any trouble.” Cas wheezed out, spluttering a little as it became significantly harder to breathe. 

“Sorry kid, but you brought yourself a ticket to Trouble the moment you denied my very reasonable request.” Crowley returned with a sly smile, glancing around quickly to check the situation.

“Please,” Cas tried in vain to plead with the man, not sure how much longer he could hold out like this. 

“Aw, your mother raised you well. What lovely manners. How polite. But let me enlighten you Castiel, 'please' and 'thank yous' don't cut it in prison. You have to learn things the hard way.” As Crowley spat out the last few words Cas suddenly felt a piercing, searing pain in his right thigh. He cried out, although it came out as more of a breathy gasp. Crowley smiled, releasing Castiel abruptly so that he fell limp to the ground. 

Cas heaved in heavily, glancing down at the spreading deep red stain on his thigh, it hurt. A lot. 

“Gabe,“ he called out weakly, pressing down on the wound, feeling the hot, sticky liquid ooze onto his hands. 

Gabe quickly alerted the guards who were soon escorting a limping Castiel to the doctors wing. Cas smiled ever so slightly, every cloud had a silver lining right?

-

Cas' eyes slowly fluttered open in a blurry haze, he could hear a muted voice, his eyes struggling to focus for a few moments. He soon realised where he was, in the doctors room, laid out on the op table, he was obviously coming around from the anaesthetic. 

“Cas? Cas how you feeling?” Castiel slowly turned his head, the blurry haze clearing as he recognised Dean standing next to the op table, looking intently down at him. Castiel smiled fondly at the nickname Dean had apparently chosen for him, not many people abbreviated his name, but it sounded good the way Dean said it. 

“Better, thank you.” Cas replied, his voice a little slurred as the drug continued to wear off. 

“Whoever knifed you did quite a nasty job, just missed a tendon. But I've stitched you up. Should be good as new.” Dean said with a smile, patting Castiel's shoulder. 

Cas pulled himself slowly up into a sitting position. Yawning lazily, he slipped the thin linen sheet off of himself, so as to get a better look at his leg. He noted that his pants had been removed and reddened a little, suddenly feeling exposed in just his boxers. 

Dean seemed to sense his discomfort and stepped away, "sorry, about-uh, that. We had to take them off so I could access the wound.” Dean apologised, rubbing the back of his neck with his hand. Cas smiled, brushing the apology away, “don't worry about it, just hadn't realised. That's all.” He assured. 

Unfortunately, he couldn't get a particularly good look at his wound as a gauze patch covered it. “You can take that off in a few days.” Dean commented, stepping back towards Cas. “It's just there to allow it time to heal.” Cas nodded. 

“That's fine, thank you. Again.” 

The corner of Dean's mouth twitched upwards, he nodded, “you're welcome, Cas. Just uh, try and stay out of trouble okay? Last thing I want is having you leave here in a body bag.” He tried to pass the comment off as a joke, but there was a definite tone of concern in his voice. 

Cas nodded, folding his arms and sighing. “Trust me, last thing I wanted was trouble. Trouble came looking for me.” 

Dean chewed on his lip and moved towards Cas, tentatively resting a hand on his shoulder. “You know, if you tell me who did this to you, I can have them locked up in the SHU. Things like this shouldn't be brushed under the carpet.” 

Cas huffed a laugh and shook his head, “unless I want a knife to my other leg, I'm better keeping my mouth shout.” He paused and glanced up at Dean, “thanks though.”

Dean nodded, understanding. “You've only been here six days, just, try and go easy.” He dropped his hand from Castiel's shoulder. 

“I will.” Cas promised. Looking sincerely at Dean

“Hey Doc, you finished with him?” An officer interrupted, poking his head into the doctors office, and gesturing towards Castiel. 

“Uh, yes. Yes I am.” Dean shook himself a little, looking slightly flustered. The officer nodded, walking into the room. “Up you get.” He instructed, Cas obeyed. The officer handed him a new pair of pants and Cas changed quickly into them. 

“Alright, see ya Doc.” The officer said, taking Castiel's arm and leading him out the room. Dean nodded goodbye, his eyes connected with Castiel's for a brief moment, and a look of genuine affection passed between them. “Bye,” Dean mouthed with a smile; Cas returned the smile and nodded before being escorted away.


	6. Chapter 6

Castiel limped back to his cell, Gabe's face brightened visibly upon seeing his cell mate.

“Cassy!” He greeted the taller man enthusiastically, Cas smiled.  
“I'm alive.” He joked, gesturing to his leg.  
“And let's keep it that way,” Gabe said with a smile, clapping Castiel on the shoulder. “For a newbie you sure know how to land yourself in trouble.”

Cas raised his brows in agreement, flopping onto his bed with a sigh. “Looks like the Doctor fixed you up well.” Gabe noted, he was seated on the small, metal toilet in the cell. They often used it as a makeshift chair, seeing as other than the bunk, there was nowhere else to sit.

“He's a good doctor.”

“What happened to 'Mister I fancy my doctor'?” Gabe asked, quirking an eyebrow.

“Oh I still 'fancy' him.” Cas answered with a knowing smile. “Just stating that he's a good doctor. It barely even hurts anymore,” he added as an afterthought, tracing his fingers over his sealed wound thoughtfully.

“Well maybe you'll have to keep getting into scrapes, so you can see him more.” Gabe joked, Cas laughed although he couldn't deny that part of him thought that maybe that wasn't such a bad idea. “I'll never understand why'd you'd purposely come and work somewhere like this,” Gabe mused, shaking his head.

Cas murmured in agreement, wondering why exactly Dean would choose a place so brutal and wild as this to lay down his career. Maybe he liked the danger, the thrill of it all, the challenges. Maybe, for that reason, he wasn't all that dissimilar to Cas. It was the thrill and the challenge of a bank robbery that first attracted him to the notion, the complexity of it. And that was the very reason that he'd selected it as his preferred method of gaining money, money to pay for his mother's urgent need for healthcare, as opposed to drug dealing or more drastic measures.

Cas sighed dejectedly as he thought of his mother, how disappointed she must be. Of course, as soon as Castiel was arrested and his face broadcasted all over the news, Michael had come to their mother's rescue. Michael being Castiel's eldest brother, a brother who had not been in his life since he was twelve years old.

_“Why didn't you just call Castiel? I have the money. There was no need for all this.” Michael let out an exasperated sigh, Cas shook his head in disbelief, and was thankful for the restraint of the cuffs around his wrists._

_“Oh enlighten me Michael, how the hell could I have called you when I didn't even know your fucking number? Or better, whether you even existed!” Cas fired back, the pain and hurt explicit in his expression. Michael said nothing, simply shook his head in a condescending way that made Castiel, quite frankly, want to 'beat-the-crap-out-of-him.'_

_“Just tell me that mother's okay.” Castiel said bluntly._

_“Mother is well, she is receiving the medical attention she requires.” Michael responded curtly, lips pursed. “She cries about you Castiel, you've ruined her. Her precious, beloved son now going behind bars. A criminal. A killer. You really do know how to treat your mother don't you.” He hissed._

_“Do you think I wanted this? Really? You really think I fucking wanted this?!” Castiel leaned forward abruptly, his face a few inches from his brother's. “I only wanted to help her, and that was more than you ever fucking did. You hear me! You abandoned us Michael! You left us!” Cas yelled through his tears, until he was forced away by two guards, pulling him back._

And that was the last he saw of Michael. Leaving the court house after Castiel's final trial.

Castiel exhaled loudly, it was not a fond memory. Not one he enjoyed reliving. At all.

Visitation hour had been and gone each day, and as he expected, there were never any visitors for him. Cas wasn't all that surprised, he'd tainted his family's good name, and consequently, they wanted to break all ties with him. He deserved it.

However, a small part of him had hoped that perhaps Hannah would have made an effort to see him. Hannah being Castiel's sister, out of his siblings she was the one that Castiel felt most connected to, most trusting of. But, regardless, she had not made any appearance as of yet.

Of course Luce, his other older brother, was not new to spending time in prison cells. But he'd only ever been arrested for petty crimes, and so prison was more of a vacation for him than a permanent residence. Castiel didn't expect Luce to make any kind of appearance either, they had not been fond of each other while growing up.

He sighed dejectedly and shifted to his side, staring at the bland brick walls of the cell.

**Notes for the Chapter:**

> Did you like the flashback? I kinda wanna give both Dean and Cas a little more context as well as developing the plot. Again thank you for reading!


	7. Chapter 7

It has been three weeks since Castiel had first entered through the tough iron prison gates. And each day never failed to pose new challenges and experiences.

After Gadreel had heard of Crowley's attack on Castiel, he'd decided to take matters into his own hands. Consequently, Crowley ended up suffering from serious concussion (after having his head had repeatedly banged against a wall.) He didn't bother Cas again.

Castiel's friendship with Doctor Winchester also began to flourish. Dean would make each appointment last a little longer than it had to, his fingers always lingering on Castiel's skin for longer than was needed. Castiel wasn't the most patient of people, and had attempted to 'make a move' on Dean several times, but Dean always backed away and got flustered, so it never really went anywhere.

Castiel had his time occupied by other things though, Gadreel had now enlisted him to snatch things. Take possessions from other inmates. It was a very risky and very demanding task. Castiel didn't mind it per se, he enjoyed the challenge. But the challenges often posed serious threats if Castiel failed them.

-

Gadreel leaned against the wire fence, pausing before he spoke. “You see the Doc often don't you?” He asked, raising an eyebrow

“Yeah, daily, for my insulin shots.” Cas replied, meeting Gadreel's eyes with an inquisitive look. “Why?”

Gadreel smiled, “I want you to get something from him for me. His keys.”

“His what!?” Cas spluttered, “that's near impossible Gadreel, you know I can't do that.” He protested.

“You haven't failed me yet, don't let me down now.” Gadreel returned in a more menacing tone.

Cas sighed, exasperated. “He keeps his keys attached to a band around his belt loop. How the _hell_ do I get them?” Cas asked, trying his best to keep as collected as possible.

“Do whatever you have to do. But I need those keys.” Gadreel said firmly.

“And what if I can't get them?” Cas asked, fearing the worst.

“Then I find someone new.” Gadreel spat out the words, leaning in close to Cas, and Cas knew exactly what that meant.

He nodded quickly and stepped away.

“Don't let me down.” Gadreel said lowly as Cas backed away.

“I won't.” Cas assured, although he was not entirely sure how he would fulfil his promise.

-

"Cas," Dean greeted warmly as Castiel entered the doctors room.

“Doctor,” Cas returned with a smirk, and surprisingly, this time, Dean didn't look away.

“Good day so far?” Dean asked, raising an eyebrow as he carried out Castiel's insulin shot.

“It's definitely improved now.” Cas replied with a grin, Dean flushed at the flirtation.

“I'm glad to hear that.” He said, his voice quieter, a smirk playing on his lips.

Castiel's attention was suddenly directed to the keys hanging from Dean's belt loop. His eyes quickly flicked back up so as not to draw to much attention. Cas shuffled a little closer to Dean, searching his brain for ways that he could retrieve the keys.

The only way he could get those keys was by unhooking them from Dean's belt loop, and he could only do that if he was very close to Dean and even then, Dean would probably still notice. Unless, he was... distracted.

Cas thought for a moment; he wasn't entirely comfortable with using Dean as a vice to carry out Gadreel's requests. However, he also did not fancy being on the wrong side of Gadreel. He glanced up at Dean again, rattling his mind for ways he could get the keys without essentially 'using' Dean. But his mind was blank. Despite his morals having a rather intense internal conflict, Cas relented and decided he really did need those keys. 

He leaned in closer to Dean, who was standing beside the chair where Cas was seated; and without warning, he grabbed Dean's waist with both his hands.

“I want you Dean.” Cas moaned in a low voice, and it wasn't a lie, even if Castiel's motive wasn't only to suck Dean off.

“Cas!” Dean yelped in a sharp whisper.

Castiel's experienced hands deftly pulled the zipper of Dean's pants down. His fingers tugging at the waistband. As he pulled down, he attempted quickly to unhook the keys from Dean's belt loop, not quite succeeding.

“Cas stop!” Dean said firmly, rough hands pushing Castiel's hands away. Dean looked down at Cas, his expression hard to decipher, it was shock, pleasure, uncertainty, anger - Cas wasn't entirely sure.

Dean pulled his zipper back up, backing away from Cas. He looked angry now, disappointed. Cas bowed his head in embarrassment.

“Guard! Please escort the inmate away!” he called loudly.

Cas whispered a desperate apology as he was led out of the room, but it was not to array.

-

“Fuck, fuck, fuck.” Cas whispered under his breath, head in his hands.

“Tell me what happened,” Gabe pleaded with Cas, who has been sitting on the edge of his bed in the same position for the past twenty minutes now. “It can't be _that_ bad Cassy.”

Cas sighed heavily, “it is _that_ bad” he replied, speaking into his hands.

“Is the Doc married or something? Because you know-”

“Shut up Gabe! Just shut up.” Cas interjected angrily, lifting his head from his hands and pushing the smaller man away from him. Gabe lifted his hands in surrender, a little taken aback by Castiel's outburst.

“Alright, alright. Sorry I ever asked.” He mumbled, climbing back onto his bunk.

Castiel drummed his fists against his forehead, fuck, why had he done that? He knew objectively that he was over reacting to the situation, but he couldn't quite pinpoint why. Maybe he had misjudged the whole situation anyway, maybe Dean wasn't attracted to him like that all; and now Cas had completely ruined the chances of a friendship with Dean, let alone anything further than that.

Of course sucking him off was a stupid fucking idea.

“You _WHAT_?!”

Oh shit, he said that out loud.

“You sucked him off?!” Gabe jumped off the bunk to face Cas, mouth open wide in surprise and shock. “Jesus Christ, you are a wild one.”

“I didn't suck him off.” Cas mumbled.

Gabe raised an eyebrow, “sooo, you tried to? And it didn't work out?”

“Pretty much.”

Gabe clapped his hands together, “man oh man Cassy, what have you got yourself into?”

Cas rolled his eyes.

“Do you even know if he swings that way?” Gabe asked curiously.

“No, I just, well. I... Gadreel wanted me to get Dean's keys-” Cas said in a hushed voice, “so I, well I thought-”

“You thought giving him a quick'ol bj would be the answer.” Gabe finished, snickering; he could see Castiel wasn't finding any of this particularly amusing, so decided to tone down his humour for the time being. He sat down beside Cas. “What happened?”

Cas sighed, “he freaked out, I guess I should have expected that.”

“Y'know, moving from no base to third base is pretty speedy. If you really like the guy, maybe a rushed blowjob and stealing his keys isn't really the best move.” Gabe volunteered with a smile.

“I know,” Cas responded dejectedly.

“Don't dwell on it, you might have fucked up today but there's always tomorrow.” Gabe said assuringly, patting Cas on the back.

Castiel nodded, although despite Gabe's consolation he didn't feel all that better. He'd lost Dean's trust and any chance at some kind of a friendship, and he couldn't change that now. He rolled onto his stomach and buried his face into his pillow, he just needed to sleep and forget about this all. Yet again, he'd fucked up. Nothing new. 

No, it was nothing new. 

**Notes for the Chapter:**

> I dunno how I feel about this chapter, I kept redrafting it because I wasn't sure exactly the direction I wanted it to take but I think it's okay? Next chapter I'm thinking about something Dean's POV for a change... hope you enjoyed!


	8. Chapter 8

Dean pulled up into his designated parking space, yawning lazily. His days always started early.

7AM-9PM. That was his shift.

Every day was a long one, but each day was also an interesting one, and yesterday had most certainly been no exception.

As much as Dean had willed himself to stop thinking about Castiel, he had not succeeded. All he could see when he had closed his eyes the previous night was Castiel's brilliant blue eyes and his mess of brown hair. All he had dreamt about was Cas. All he could think about was Cas. And to be perfectly honest, it pissed Dean off; he didn't want to think about him, especially not after yesterday.

But then again...

No. Dean quickly shook the thoughts away, he was not about to justify this _inmate's_ actions. What he had done was wrong, even if Dean hadn't exactly minded it...

He sighed heavily as he looked at the foreboding building that practically served as his second home. He opened the car door and stepped out, brushing himself down. Time to get to work.

-

Dean couldn't help the ball of anxiety building in his stomach as Castiel's designated time slot approached. He wasn't exactly afraid of the man in the conventional sense of the word. Cas didn't scare him, but he made Dean feel vulnerable. Whenever he was around him the lines blurred, and he felt...different.

He hadn't been in a long term relationship for over two years now, so asked himself whether perhaps Cas was some kind of delayed rebound. He couldn't deny his attraction to Castiel, but also couldn't work out why he was so attracted to him. What it was about the man that made him so god-dammed enchanting.

It wasn't like Dean was avidly looking for someone, he was perfectly content with his one night flings- both with men and women, that happened on roughly a monthly basis. He didn't need anything more than that...did he?

“Uh, Doctor Winchester?”

Dean snapped out of his thoughts and turned quickly.

“Yes?”

“Castiel Novak's here for his appointment.” The guard said, pushing Cas into the room. “I'll just be outside.”

Cas didn't look at Dean as he walked into the room, his eyes planted firmly on the ground in front of his feet, as he walked across towards the chair, sitting down in silence.

This was very different to the Castiel that Dean knew, the Cas that always had a witty one-liner or a cheesy flirtation.

Dean walked across to the medicine cabinet, the sound of his footsteps  
almost seemed to be amplified in the silence. The atmosphere between them was stifling, so thick is was almost tangible. So many unspoken words and feelings filling the space between them.

“Dean -”

“Cas -”

They both stopped.

“You first,” Dean said as he fixed up the shot, turning to face Cas.

“About yesterday, I'm sorry I did that. It was totally out of line.” Cas apologised, and suddenly Dean wasn't all that angry anymore, he smiled at Cas.

“Apology accepted.” He replied cheerfully.

Cas sighed in relief and smiled at Dean, stretching out his arm so Dean could administer the shot.

Dean took Castiel's arm; and despite the fact that this was a purely medical procedure he couldn't help but be acutely aware of the heat of Castiel's skin against his finger tips. Neither could he ignore the fact that Cas was gazing up at him, unflinchingly so. Yet neither things made Dean uncomfortable, they just made him feel...

“This might be out of line, but could  
I ask you a personal question?” Cas broke Dean's line of thought, quirking an eyebrow as Dean patted down Castiel's arm.

Dean paused before responding, unsure of what Castiel's intentions were.

“Shoot,” he said decidedly, it wasn't like he'd have to answer the question anyway.

“Do you uh, do you like guys?”

Dean's jaw tightened, his eyes meeting Castiel's. He knew the meaning behind that question.

“Cas, you know it's against every rule in the book for me to do anything with an inmate.” He said with a sigh.

Cas looked down, a flush spreading across his cheeks. “Yeah, I know.”

“You seem like a great guy, from the little I know of you. And if things were different...” Dean stopped himself, suddenly feeling very conscious of his feelings, and his very definite attraction to Castiel. He didn't know how to go on, because in all honesty, he didn't want things to be different. He wanted this Castiel, the Cas who was locked up behind prison bars. And nothing could change that.

Cas looked up, seeming to understand Dean's unspoken feelings. He leaned forward and impulsively, he pressed his lips against Dean's.

Dean froze, unresponsive.

“Cas, Cas we can't-”

Cas moved in again, reaching his hands out to cup Dean's face, his mouth cutting off Dean's half-hearted protests, the kiss was longer and deeper this time.

There was a drum against the door. “You nearly finished Doctor Winchester?” The guard sounded.

Dean broke away from the kiss with a start, wiping his mouth with his coat sleeve.

“One moment!” He called back, staring intently at Cas.

“This could never work,” he whispered desperately, searching Castiel's face.

“Yes it can.” Cas responded firmly, before standing up. He softly took Dean's hand in his own. “It can.” He repeated, before dropping Dean's hand and walking out towards the door.

Dean's eyes were fixed on Cas as he left the room.

“Shit.”

-

“I'm totally fucked Sammy,” Dean said with a slur, beer bottle in hand. He wasn't one to drink away his problems but currently he did  
not want to deal with them either.

“Dean, this is your sixth bottle. Take it easy.” Sam said a he prised the bottle from Dean's fingers. “You wanna tell me what's wrong?

Dean let out an exasperated sigh. “Ugh Sammy why'd you lemme drink in the first place?”

Sam rolled his eyes, “Dean I invited you over for drinks, I didn't know you'd be having an existential crisis at the same time.”

Dean groaned again, “it's not that, there's this guy.”

“Go on.” Sam encouraged.

“He's at work.”

“One of your colleagues?” Sam asked.

“No.”

“Oh.” Sam said knowingly. “Dean, that's a problem.”

“Tell me about it!” Dean said with a groan, throwing his arms in the air.

“What's going on here?” Jess asked as she walked into the living room, grinning at how dramatic Dean was being and raising an eyebrow at Sam.

“Dean has a problematic crush.” Sam answered with a teasing tone. Jess laughed and clapped her hands together.

“Typical Dean. You always go for the bad ones don't you?”

“Literally.” Sam said with a grin, Dean groaned and playfully pushed Sam away.

“It's not funny.” He retorted with a sigh.

Sam gave Dean a friendly rub on the back and smiled, “I think we should sober you up otherwise you'll be going into work with a nasty hangover tomorrow.”

“It's my day off tomorrow.” Dean said with a yawn.

“I still think you could do with a glass of water.” Sam replied with a smile.

Soon Dean was sound asleep, sprawled on Sam's sofa with a blanket laid across him. Jess of course snapped a few pictures so as to make sure Dean never forgot this moment. And then left Dean to his subconscious thoughts and feelings, which were all very confused and very muddled.


	9. Chapter 9

“So, the keys?”

Cas glanced up, pressing into his greyish portion of mashed potato with his fork.

“I haven't been able to get them yet.” He mumbled.

“Why not?” Gadreel demanded through gritted teeth, leaning forward.

“Things didn't work out how I planned for them to.” Cas replied with a sigh.

“I want those keys Castiel.”

Cas sighed in exasperation, pushing his plate of food away. “I know, just... give me time. Okay?”

Gadreel sat back, folding his arms together. “Two days.”

“Fine.”

“And if you fail to produce them, you better pray to all your gods Castiel, I swear-”

“Castiel Novak!?” A guard interrupted loudly, shouting over the rumble of chatter in the dining hall.

Cas stood up, brows furrowing together in confusion. “Yes?” He identified.

The guard strode towards him, “you have a visitor.” He said shortly, taking Castiel's arm.

“But...it's not visitation hour?” Cas replied, confused.

“Look Novak. You have a visitor. Now do you want to see them or not?” The guard asked as he lead Castiel away from the table; Castiel could feel the heat of Gadreel's stare as he was taken away. This wasn't over.

Cas hadn't yet been to the visitation area, and so it was all new to him. There was a swift pat down before he was lead through a door and into the room.

Small tables with a chair on either side of them were placed in a structured order all around the room. However only one chair was occupied, and the person that occupied it...

“No,” Castiel muttered under his breath.

“You have ten minutes.” The guard said firmly, gesturing for Cas to sit down on the other end of the table.

Cas stood frozen in place, why...why the hell was he here?

“Novak, move.” The guard pushed Cas forward. Cas sat down heavily on the chair, staring at his hands which were clasped firmly together.

“Michael.”  
He said, his voice low and gruff, not bothering to look up at his visitor.

“Castiel, please don't be childish. This is important.” Michael returned.

“Is this some kind of joke?” Cas looked up, his eyes cold. “You think it's okay to just stroll in here and request a visit with me? What the fuck were you thinking?” Cas spat the words back at him, each syllable practically reeking with hate.

“Castiel-”

“I don't want to talk to you.” Cas interrupted, standing up suddenly, his chair grating across the ground with a screech. He turned to walk away, this was just some sick joke; just a fucked up way of Michael feeding his superiority complex. Cas wasn't going to allow him to indulge in it any further.

“Castiel! Mother... mother she's... she's dead. Castiel, she's gone.”

Cas froze.

“Castiel please,” Michael pleaded, and for once Cas could hear a crack of genuine emotion in his voice.

He turned slowly to meet his brother. “What?” his voice came out as barely a whisper.

“I'm so sorry Castiel. I didn't want to tell you like this. She passed yesterday evening.”

A cloud of emotion blurred Castiel's vision, “she can't be.”

“I'm sorry Castiel. I wanted you to hear it from me rather than someone here. She...she sent her love. Before she passed.” Michael said, trying to maintain a calm and collected tone.

Cas suddenly felt very empty. Cold. Devoid of feeling.

He couldn't do this. Not now. He walked briskly back towards the guard, head down. Michael's voice and all other noises merging into the background. His mother meant everything to him, in an abusive home she had been Castiel's place of refuge. She'd always been there for him, with a comforting word or a welcoming hug. Throughout his whole life she had never doubted him,  never stopped loving him; no matter how much he fucked up. And now she was gone. She was gone. 

Now, nothing mattered.

None of it mattered. 

-

Cas rammed his fist into the wall.

Again. And again. And again.

“Cas, please. You need to get some rest.” Gabe said softly

And again.

“Cas. Please.”

The cell's were dark, only lit by the few dim lights throughout the corridors.

Night was when the wing was the quietest. The only sounds interrupting the silence being the heavy breathing of inmates as they slept, and the echo of footsteps as the guards carried out their night shift.

Today a new sound joined them, the soft thud and crack of knuckles colliding with brick.

Then it stopped.

Cas fell down in a crumpled heap, wracked with emotion.

He didn't get into bed that night, eventually falling asleep on the cold stone floor, his body curled into the foetal position.

He never got to say goodbye to her.

**Notes for the Chapter:**

> I apologise for the angst! I promise it won't stay like this for too long. Are you guys still enjoying the story? Thank you for reading.


	10. Chapter 10

**Notes for the Chapter:**

> This chapter is really short, for some reason I can't ever seem to write long chapters for fics. Just seemed like a good place to end it? But hey, hope it was good to read :)

Dean wasn't going to repeat his mistake. His day off had allowed him to see things clearly, and he was certain now that he wouldn't be sucked back into Castiel's charm.

He was going to remain professional and responsible. Nothing more.

And so as Castiel stepped into his office, Dean intended on being exactly that. He was going to tell Castiel that this- whatever it was- had to end, it wasn't right, and it could never go anywhere. He ran through his planned speech in his head, turning to face Castiel. He saw him and stopped.

Cas looked so... utterly broken.

The bounce in step and the life in his eyes had faded away.

_Jesus, it had only been one day. What the hell had happened?_

Castiel moved silently to sit down in the chair, stretching out his arm  
for Dean. His face expressionless.

As Dean sat down beside Cas to administer the shot, his eyes caught sight of the raw and bruised skin of knuckles.

“Cas, what happened?” Dean spoke tenderly, resting a hand on Castiel's wrist.

Castiel's jaw clenched, fixing his gaze straight ahead, his eyes becoming glassy.

“Cas?” Dean leaned in, searching the other mans face.

Cas let out a ragged sigh, “my mother died.” He breathed out in one go, looking quickly down.

“Oh God. I am so sorry.”

Cas shook his head slowly, “so am I.” He said in a small voice. “I never...I never even got to say goodbye. I never said goodbye to her Dean.” He looked up at Dean, eyes brimming with tears.

Dean didn't have the words to adequately express his sorrow for Castiel's loss. So simply pulled him in for a hug, wrapping his arms tightly around Cas. It was completely crossing the lines of 'professional,' but Dean couldn't have cared less.

They stayed like that for a few moments, the warmth of their bodies, a gentle comfort to one another.

It wasn't until the guard seemed to have something of a coughing fit outside that Dean suddenly remembered where they were, and was brought back to his senses.

He pulled back slowly from Cas, the concern and care in his expression was genuine and comforting.

“It does get better,” he murmured softly, resting a hand on Castiel's shoulder.

Castiel gave a small nod in response, he stood up and looked as if he was about to say something, but, no sound was heard. He walked towards the door, whispering a hushed goodbye, and left.

Dean stood for a few moments. A realisation slowly dawning upon him. He cared about Castiel.

He really cared about him.

And suddenly, nothing else really seemed to matter. Not his job, not his reputation. Nothing. Castiel mattered, and he mattered a lot. And Dean couldn't shake that.

He sat down and clasped his hands together. This was bad, this was really bad. And yet, it was simultaneously so amazingly good. Castiel had awakened something in Dean, something real, something special.

_But he's an inmate. He's a criminal Dean._

He ran a hand through his hair, his thoughts spiralling out of control.

He'd fallen head first for Castiel Novak. And he wasn't at all sure what to do about that.


	11. Chapter 11

**Notes for the Chapter:**

> The chapter shifts to Dean's POV half way through, just as a heads up. Hope you enjoy the chapter :)

“Shit.” Cas awoke with a start, eyes  
blinking open.

“What's up with you?” Gabe asked from the toilet, slightly surprised as Cas had barely said anything in the past two days.

“I haven't got the keys. For Gadreel.” Cas responded with an exasperated sigh.

“Uh-oh.”

“Shit. Fuck.” Cas cursed angrily, his grief temporarily subsiding as he wondered how he could possibly worm his way out of his predicament.

“Avoid Gadreel at all costs.” Gabe said solemnly as he flushed the toilet.

“Thank you, Einstein.” Cas replied, rolling his eyes.

Gabe grinned as he stood up  
to wash his hands. “At least it's livened your spirits a little.” He offered.

“Hardly.” Cas retorted, carding his fingers through his hair and sighing. “God, I really know how to fuck up my first month of prison don't I?”

Gabe dried his hands off on his pants and sat down beside Cas. “Think of it more as a learning curve Cassy.” He suggested.

“I just keep making more mistakes, I'm not learning anything from  
them.” He mumbled dejectedly. His thoughts turned to his mother once  
more, she would have wanted him to serve his sentence responsibly, keeping out of trouble; and that was the very opposite of what he was currently doing.

Yet again, he'd let her down. Simply proving to everyone what a terrible mistake he was.

“Just watch your back and you'll  
be fine.” Gabe interjected his line of thought. Cas nodded slowly, head hung low. Gabe gave him a soothing pat on the back and then went back to occupying himself with various tasks. Leaving Cas to his conflicting and colliding thoughts, his inner morals battling once again.

-

“Hannah? Hannah is that you?” Cas spoke into the receiver, trying to make sense of the muffled speech at the other end of the line.

He was leant against one of the many phone booths that were stationed around the perimeter of the outdoor grounds. Each call was limited to a few minutes, and that was all Cas needed. He just needed to hear his sisters voice again.

“Castiel?” A voice sounded from the speaker, slightly crackled.

Castiel's face lit up in a smile, he pressed the phone closer to his ear. “Yes, Hannah, it's me. I, I uh, I wanted to call you. I miss you. Are you okay? How is everyone?” His words came out in a kind of hurried blur; as was of expected of someone who had so much to say and so little time to say it. The sound of Hannah's voice was so comforting, a gentle familiarity; and yet a painful  
reminder of the distance between them.

“Castiel, it's good to hear your voice. I'm well, a little tired. And we're coping, thank you. How are you? How's prison?” Hannah's voice answered, her warm and caring tone suddenly reminding Castiel of their mother.

“Good, good. I'm glad to hear that. And prison it's uh...it's as good as it can be.”

“Are you staying out of trouble?” Hannah asked, and it wasn't in a chiding or disapproving way, Cas knew she was genuinely worried for him.

“Yes. Yes I'm fine Hannah. Don't worry about me.” He assured her.

There was a pause on the other end of the line, “I'm going out later with Michael, to work out arrangements for mother's funeral. I'm sorry you can't be there Castiel. You know she loved you so much; she even wanted to visit you here, she missed you. Just...Michael never let her, always made excuses. I'm sorry Castiel.”

Cas faltered a little before replying, gulping back the knot of emotion in his throat. “Thank you Hannah. That...it means a lot.” His voice cracked.

There was a sigh on the other end of the line. “I miss you Castiel.”

“I miss you too.”

As Cas spoke the last word a heavy hand descended on his shoulder.

“End the call.” A gruff voice said behind him.

“Hannah, I have to go. I'm sorry. I'll call soon. I love you.” Cas said hurriedly into the receiver.

“I lo-”

The receiver cut off, the inmate behind him apparently deciding that his call had gone on long enough.

Cas turned to face the owner of the voice behind him.

“Gadreel.”

“Hello Castiel. So sorry to interrupt you, but let's cut to the chase. Where are the keys?” Gadreel fixed Castiel with a fierce stare, holding out his palm.

Cas tightened his jaw, preparing himself for the worst. “I don't have them.” He replied monotonously.

“What? Castiel, correct me if I'm wrong, but did I or did I not give you two days to retrieve those keys?” Gadreel leant forward, grating his teeth together.

“You did. But, I can still get them, I have an appointment today and-”

"No, no more bargaining Castiel." Gadreel shook his head slowly, he lifted his hand, making a small gesture that Cas didn't recognise. And before Cas had any real time to register what was going on, there was suddenly a whole swarm of inmates charging right in his direction.

The next few minutes (which felt more like hours) passed in a blur. Cas felt himself being pushed to the ground and then sharp jolts of pain coming from every exposed region of his body.

And then. Darkness.

-

“Doctor Winchester?” Dean's walkie-talkie suddenly sounded. The walkie-talkie's were never used unless of emergencies.

“Yes? Speaking?”

“Doc, we've had an attack on an inmate, he's in a pretty bad way. We're escorting him up to your wing now. Could you have a bed ready for him?”

“Yes, I'll arrange for that now. Could I have the inmate'a name for a back up check, in case he has a medical condition I should know about.” Dean asked, as he signalled for a nurse to make up a bed in the infirmary that was located just outside of his office.

“Castiel Novak is the inmate's name Doc.”

Dean gasped. Shit. He shook himself, trying to remain professional. “Th-thank you.” He breathed out shakily, before setting the walkie-talkie down.

He fell down heavily into his chair, trying to collect his thoughts and push his feelings to the side. He hoped to God that Cas was okay.

-

Cas looked in a bad way, a really bad way.

 

Dean was sat down in the chair beside Castiel's bed, it had been a six hours since Cas had been escorted to the infirmary. He'd assured the prison officers that he would be able to handle the situation, along with the help of the nurses.

He'd administered some pain relief and a few other drugs, as well as closing a few wounds and bandaging up a few others.

Castiel's face was bruised and bloodied. His left cheek and eye swollen and disfigured. Deep purple bruises marking his skin.

But Cas wasn't easily broken, he was still alive, still breathing. Now, Dean just had to wait for him to wake up.

As the end of his shift grew nearer, Dean felt a pang of worry in his chest. He didn't want to leave Cas. Not like this, unconscious and alone. What if he woke up? And Dean wasn't there.

He glanced anxiously at his watch.

Only twenty minutes left.

He stroked Castiel's arm tentatively, brushing his fingertips across the smooth skin. “Please wake up Cas,” he whispered, looking down at the man. Even like this, all beaten and bloodied, Dean couldn't help but appreciate just how attractive Castiel was.

There was a knock on the door, abruptly reminding Dean where he was, sprinting back into reality, he walked up to answer it; one of his assistant nurses stood behind the door. “I have the full witness report of the events that led to the inmates condition.” She gestured in Castiel's direction, handing Dean a file. “Thank you.” Dean smiled tiredly, taking the file.

“Is your shift not over yet Doctor Winchester?” the nurse asked, Dean was clearly doing a poor job at masking his tiredness.

“Almost, I-”

“Dean?” a small voice sounded from behind him.

Dean spun around, striding quickly over to Castiel's bed. “Cas, you're awake.” Dean smiled broadly, looking fondly down at Cas. The nurse appeared to take that as her cue to leave and closed the door behind her.

Dean sat down on the chair, watching as Cas slowly adjusted to being awake. He'd been out for several hours.

“How're you feeling?” Dean asked.

“Like I've been beaten up.” Cas joked, shifting a little to get a better angle of Dean, and immediately regretting his decision, he groaned in pain. “Everything hurts.” He muttered.

“You took a pretty good beating.” Dean replied, “it'll take you at least two weeks to be over the worst of it.”

“I'm going to be in here for two weeks?” Cas asked.

“Yup. Doctors orders.” Dean winked at Cas.

“Well aren't I a lucky guy?” Cas said with a smirk. “Waking up to your face every day, what more could a man ask for?”

Dean blushed and smiled, glancing at the time. “My shift is about to finish, but I promise I'll be here back and early in the morning. And there'll be a nurse checking in on you if you need anything.”

Cas nodded, he reached out for Dean's hand which was resting on the side of Castiel's bed. Without really thinking, Dean took Castiel's hand in his own, giving it a gentle squeeze.

“And you have company,” he added, indicating with his eyes the other occupied beds in the infirmary.

“Ah yes, murderers and rapists, Great company.” He winked.

“Sure you'd fit right in.” Dean joked, giving Castiel's hand a teasing squeeze. “Prison jokes aside, I really have to leave now.” He mumbled.

Cas heaved out a long sigh, sticking his bottom lip out. “Do you have to?” He pleaded.

“Unfortunately so. They don't provide beds for the staff.”

Cas shifted to the right side of the bed and patted the space beside him. “Always room for two.” He winked.

Dean raised his eyebrows, “I think that might be a bit risky.” He joked.

“We're in prison. It's all about taking risks.” Cas shot back with a devilish grin.

“As nice as the offer is, I'll have to pass.” Dean grinned back, gently untangling his hand from Castiel's and standing up. “Now you get some more rest, and don't move around too much and you'll be just fine.” He directed, his voice taking on it more professional tone.

“Of course Doctor Winchester.”

Dean smiled, “see you in the morning Cas.”

“See you Dean.”


	12. Chapter 12

As the days passed Castiel slowly began to recover; his bruises fading and his wounds closing. Dean spent as much time as was possibly allowed by Castiel's side, sometimes just sitting beside him as he slept, Dean treasured those quieter moments.

He could not deny now that his attraction to Castiel was more than simply physical, Castiel was enchanting, exciting and he had awakened something in Dean. Dean had even looked through Castiel's case file, in the hopes that perhaps that would dissuade his feelings, but quite the contrary.  When Dean learnt that Castiel had broken the law in his mother's aid it only served to make Castiel even more appealing in his eyes.

He was fully aware that if he acted on his feelings (which he very much wanted to) and was found out, the consequences would be serious and unforgiving. But the doubt that crept into his mind whenever he considered his situation, was quickly pushed aside whenever he saw Castiel's face broke into smile, to Dean, Cas was worth losing everything.

Of course, they had to be careful, they hadn't engaged in anything too serious as of yet (one, because Cas physically wasn't able to; and two, because they had an audience) but on more than one occasion and inmate in the infirmary had questioned the looks Cas and Dean exchanged with one another and the not-so-subtle touches.

When the lights were switched out Dean would hurriedly press his lips against Castiel's before leaving, luckily, it wasn't noticed. But Dean yearned for more, not just physically but emotionally; he wanted to take Castiel out, talk to him like he wasn't just his patient. Just be _together_ with him; but of course, that could never be a reality.

Castiel had now spent 6 days in the infirmary, upon Dean's order's he was transferred to the patient bed in Dean's office - in order that Dean could watch his recovery 'more closely' and so Castiel could get some more quiet as the other inmates had been 'disturbing him.'

And so when Dean strolled into his office and saw Cas sitting up on the bed, apparently awaiting his arrival, he was more than happy.

“Dean,” Cas greeted with a warm smile.

“Heya Cas,” Dean beamed back, hanging up his coat and setting down some papers. “How you feeling this morning?” He pulled a chair over beside Castiel's bed and sat down, Cas angled his body to face Dean.

“A lot better actually, everything is a lot less sore.”

“I'm very glad to hear that,” Dean said leaning in towards Cas.

“My lips are still kinda sore,” Cas said with a smirk, his tongue swiping out across his lips.

“Oh really? You want me to help with that?” Dean asked lowly.

“If you could, Doc.”

Dean didn't need any more teasing, he pushed his lips against Castiel's, pulling Cas closer into himself. The kiss was passionate, almost violent, the pent up frustration in them both finally given a release.

After a few minutes of their tongues in each other's mouths and a lot of touching and feeling: like a pair of horny teenagers, they broke away. And God, if Dean already thought Cas looked fucking kissable, he looked fucking perfect now. His lips pink and swollen and wet, Dean couldn't help the growing hardness in his pants.

Cas' eyes were dark with lust and want, “is the door locked?”

“Fuck, uh, let me check. Need to see my uh schedule as well.”

Dean quickly consulted his schedule, he wouldn't be needed for another hour, of course that was excluding emergencies, fuck, there better not be any emergencies. He pulled at the door handle. Locked. He threw a glance back at Cas, who had now thrown the sheet off of himself, legs open, revealing a very prominent bulge at his crotch. Dean moaned.

“You're going to get me into so much trouble,” he whispered huskily as he walked towards Cas.

“Mm but you like that don't you? Being bad. Breaking the rules...” Cas smirked, pulling Dean closer, until he was sitting on the bed.

“Maybe a little,”

“We're more alike than you think.” Cas murmured, leaning in to peck Dean's lips.

Dean shifted closer to Cas, moving his hands to rest on Castiel's thighs.

“This is so, so illegal.” He said quietly, his hands creeping up Castiel's thigh. Cas smirked, wrapping his arms around Dean to bring him closer, “not all illegal things are bad you know,” he whispered into Dean's ear, brushing his lips against it.

Dean smiled, “I know.”

He clashed his mouth against Castiel's once more, his hands sliding underneath Castiel's top. The constant risk and threat of their predicament made it all so much more exciting and arousing for Dean. His heart was practically beating out of his chest when Cas removed his top, both from the risk of being discovered and because Cas was fucking hot.

“Take yours off.” Cas pleaded, pulling at Dean's shirt. With deft fingers Dean quickly unbuttoned and slipped out of his shirt, before firm hands were pulling him down onto the bed.

Dean lay on top of Cas, the skin on skin heat was electrifying. He grinned down at him, panting slightly, “you're so fucking hot.”

Cas grinned back, quickly rolling so that he was positioned over Dean. “Oh you do make me blush.” He replied with a smirk.

He began planting small kisses down Dean's neck and along his collarbone, and as he did so started slowly rolling his hips right against the pressure in Dean's pants. Dean moaned, his own hips bucking a little, seeking friction.

“Patience,” Cas smirked, planting more kisses down Dean's chest.

He continued down with his path of kisses until he came to the top of Dean's waistband, he looked up at Dean and cocked an eyebrow, Dean nodded. Cas smiled, his fingers slowly curving round the top of the waistband as he tugged down. Dean lifted his hips a little to help until his work trousers were in a dishevelled heap on the floor.

Dean certainly wasn't small, his 7 inches prominent, even through the fabric of his boxers. Cas moaned softly as he kissed Dean through his boxers, he'd wanted to do this for so long, just be like this with Dean. He'd practically given up all hope, hell, he still thought he was dreaming. This was just too perfect.

He became more needy, practically sucking the material of Dean's boxers, until Dean was a writhing mess beneath him, begging Cas to take them off.

“Okay, big boy.” He said with a smirk, pulling down Dean's boxers in a swift movement. Dean's cock wasn't fully hard but it was still impressive. “You have a really nice cock Dean.” Cas said with a smirk, sticking out his tongue and licking his lips.

“Why don't you put that filthy mouth of yours to work.” Dean said huskily, and Cas didn't need to be told twice. He wrapped his lips around the head of Dean's cock and slowly went down until the head was grazing the back of his throat, before lifting back off and repeating the sequence.

He continued that for a few moments before getting his tongue involved, licking the veins on the underside of his cock and tasting the beads of precome that were gathering on the tip.

As he continued teasing and sucking and licking he could feel Dean getting closer, his hips involuntarily bucking into Castiel's mouth (luckily Cas' gag reflex barely existed anymore.)

“Fuck! Cas!” Dean panted with a moan as he came thick and heavy into Castiel's mouth.

He rested for a few moments in the afterglow of his orgasm before he could feel Cas slowly crawling on top of him. “Wanna help finish me off?” he mumbled into Dean's ear, raising an eyebrow.

“I wouldn't say no.” Dean smirked.

“What are you waiting for them?” Cas teased.

Dean made quick work of removing Castiel's pants and boxers, taking his cock into his hand and giving it a few quick pumps before repositioning himself to take Cas into his mouth.

He prided himself in his blowjobs, having being told many a time that he had an amazing mouth, and from the noises he was making, Castiel didn't seem to disagree.

It didn't take long for Cas to climax, Dean swiped his tongue across his lips to catch the remainder of Cas' come, he smiled up at him. “Good?”

“Amazing.”

Dean grinned, his eyes flicked to the clock, suddenly being drawn back to reality.

“Shit, Cas, we need to clean up.”

“No time for anything else?” Cas complained with a pout.

“Nada. Not right now anyway.”

“Damn,“ Cas muttered as he reached for his boxers.

“Later. I promise.” Dean said softly, planting a kiss on Cas' forehead.

“Later,” Cas affirmed with a smile.

**Notes for the Chapter:**

> Okay, I don't know if I like this chapter but I've been so busy and wanted to get it done. Apologise for the badly written smut. Thanks for reading :)


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